CA2810162A1 - Agents antimicrobiens - Google Patents

Agents antimicrobiens Download PDF

Info

Publication number: CA2810162A1
Authority: CA; Canada
Prior art keywords: alkyl; aryl; heteroaryl; cycloalkyl; independently selected
Prior art date: 2010-06-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA2810162A

Other languages

English (en)

Inventor

Edmond J. Lavoie

Ajit Parhi

Daniel S. Pilch

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Rutgers State University of New Jersey

Rutgers Health

Original Assignee

University of Medicine and Dentistry of New Jersey

Rutgers State University of New Jersey

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2010-06-09

Filing date

2011-06-09

Publication date

2011-12-15

2011-06-09 Application filed by University of Medicine and Dentistry of New Jersey, Rutgers State University of New Jersey filed Critical University of Medicine and Dentistry of New Jersey

2011-12-15 Publication of CA2810162A1 publication Critical patent/CA2810162A1/fr

Status Abandoned legal-status Critical Current

Links

239000004599 antimicrobial Substances 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 389
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239000000651 prodrug Substances 0.000 claims abstract description 80
239000000203 mixture Substances 0.000 claims abstract description 17
125000003118 aryl group Chemical group 0.000 claims description 690
125000001072 heteroaryl group Chemical group 0.000 claims description 687
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 641
125000000217 alkyl group Chemical group 0.000 claims description 536
-1 nitro, sulfo Chemical group 0.000 claims description 387
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 361
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125000005843 halogen group Chemical group 0.000 claims description 247
125000004104 aryloxy group Chemical group 0.000 claims description 245
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 231
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 229
125000000753 cycloalkyl group Chemical group 0.000 claims description 212
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 195
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 74
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KNIWPHSUTGNZST-UHFFFAOYSA-N polymyxin E2 Natural products CC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O KNIWPHSUTGNZST-UHFFFAOYSA-N 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
201000007094 prostatitis Diseases 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
229940107568 pulmozyme Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000012217 radiopharmaceutical Substances 0.000 description 1
229940121896 radiopharmaceutical Drugs 0.000 description 1
230000002799 radiopharmaceutical effect Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
229960002530 sargramostim Drugs 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
231100000019 skin ulcer Toxicity 0.000 description 1
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000015393 sodium molybdate Nutrition 0.000 description 1
239000011684 sodium molybdate Substances 0.000 description 1
TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 1
239000007892 solid unit dosage form Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
230000001975 sympathomimetic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
229960001685 tacrine Drugs 0.000 description 1
YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
FJNQWGIYSKYMRU-UHFFFAOYSA-N tert-butyl 1,2-dihydroisoquinoline-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC(C)(C)C)NC=CC2=C1 FJNQWGIYSKYMRU-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960002180 tetracycline Drugs 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
MZIYQMVHASXABC-UHFFFAOYSA-N tetrakis(ethenyl)stannane Chemical compound C=C[Sn](C=C)(C=C)C=C MZIYQMVHASXABC-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 1
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
230000035899 viability Effects 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
238000003260 vortexing Methods 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000009637 wintergreen oil Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA2810162A 2010-06-09 2011-06-09 Agents antimicrobiens Abandoned CA2810162A1 (fr)

Applications Claiming Priority (9)

Application Number	Priority Date	Filing Date	Title
US35310710P	2010-06-09	2010-06-09
US61/353,107		2010-06-09
US35540810P	2010-06-16	2010-06-16
US61/355,408		2010-06-16
US37275510P	2010-08-11	2010-08-11
US37277010P	2010-08-11	2010-08-11
US61/372,755		2010-08-11
US61/372,770		2010-08-11
PCT/US2011/039839 WO2011156626A1 (fr)	2010-06-09	2011-06-09	Agents antimicrobiens

Publications (1)

Publication Number	Publication Date
CA2810162A1 true CA2810162A1 (fr)	2011-12-15

Family

ID=44514955

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2810162A Abandoned CA2810162A1 (fr)	2010-06-09	2011-06-09	Agents antimicrobiens

Country Status (3)

Country	Link
US (1)	US8933096B2 (fr)
CA (1)	CA2810162A1 (fr)
WO (1)	WO2011156626A1 (fr)

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2011
- 2011-06-09 CA CA2810162A patent/CA2810162A1/fr not_active Abandoned
- 2011-06-09 US US13/702,936 patent/US8933096B2/en not_active Expired - Fee Related
- 2011-06-09 WO PCT/US2011/039839 patent/WO2011156626A1/fr not_active Ceased

Also Published As

Publication number	Publication date
US8933096B2 (en)	2015-01-13
US20130116278A1 (en)	2013-05-09
WO2011156626A1 (fr)	2011-12-15

Publication	Publication Date	Title
CA2810162A1 (fr)	2011-12-15	Agents antimicrobiens
WO2011159926A1 (fr)	2011-12-22	Agents antimicrobiens
US9227966B2 (en)	2016-01-05	Antimicrobial agents
US8741917B2 (en)	2014-06-03	Benzo [C] phenanthridines as antimicrobial agents
US9102617B2 (en)	2015-08-11	Antimicrobial agents
JP4580556B2 (ja)	2010-11-17	抗腫瘍薬である新規インデノイソキノリン類
CN102603628B (zh)	2016-08-17	作为抗癌试剂的喹啉衍生物
JP4412586B2 (ja)	2010-02-10	エポネマイシンおよびエポキソマイシン類似物およびそれらの用途
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